I finally got to take my first vacation of 2020 and it was everything I’d hoped it would be and more. I’ve never lived especially far from the Catskills but always opted for beach/international destinations instead of local ones. If there’s a silver lining of the pandemic, it’s that it encouraged me to do more exploring where I am.
After ~3 weeks of rapid planning, Max and I packed up the car and headed up to the Catskills for what turned out to be an amazing weekend. Visiting in the fall when the leaves are changing was so beautiful but I could see it being a great destination for hiking in the summer or a cozy cabin getaway in the winter.
Where to Stay
We stayed at Hotel Dylan for our weekend trip and it was incredible. It’s a boutique hotel themed around Woodstock with rooms named after 60’s musicians.
All of the rooms have cool wallpaper, Smeg mini-fridges, and record players complete with a selection of vinyl to play while hanging out. Although the vibes were late 60’s the rooms had some very important modern touches like a heater in the bathroom which was amazing to come home to after a cold hike.
The west side rooms are a little older and a little more kitschy whereas the east side rooms (where we stayed) are more modern boho and newly renovated. In case you couldn’t guess from the photo above, we stayed in The Bowie.
During non-COVID times you can hang out in the on-site pool or in the lobby which has the cool hanging chairs pictured below or grab a game or records to bring back to your room. When trying to social distance you can still take advantage of the fire pits outside. They build fires on the weekends and provide each room with a bag of s’mores supplies. Nothing like a roasted marshmallow to end a perfect summer day or fall night. We had such a great stay and I’d love to go back there one day.
P.S. They have 2 suites and 1 dog-friendly room as well!
What to Do
Explore the Great Outdoors
The best thing we did during our trip was hike the Giant Ledge. It’s a steep, rocky climb to the top so definitely not for someone who doesn’t have great balance but the views from the top were so beautiful. I’ll let the pictures speak for me. If you want to check it out, you can find parking around 1300-1566 Oliverea Slide Mountain Rd. You’ll know you’ve found it when out of nowhere there’s suddenly no parking on the side of the road.
If you want to get outside in a less intense way head over to the Ashokan Reservoir for a nature walk or bike ride. We parked off Route 28 between Van Dale Road and Williams Lane (there will be signs) and walked the West Basin. If you’re facing the water turn right and start walking and you’ll come across this beautiful path right on the reservoir (pictured right). We only walked about a mile before turning back but it goes for miles depending on how far you want to go and how much time you have to spend.
Depending on how much time you have, you can also check out Kaaterskill Falls, among other local hikes. In case you needed another reason to love Hotel Dylan, our room had a great guidebook for the local hikes with detailed parking directions and difficulty levels.
Drink at a Local Brewery
Unfortunately, most of the breweries were take-out only at the time, but in post-COVID times I’m sure it’s a great time. There are a ton in the area but the two I’d most want to go back to check out are Sloop and Suarez.
Where to Eat
The best meal you’ll have in the Catskills is probably at Cucina. It’s the local nice Italian restaurant with a beautiful porch and a great atmosphere. Definitely make a reservation and get the sausage pasta.
We had a great lunch at Tinker Taco Lab on our last day. Max got a margarita with ginger, pineapple, and more that was excellent and the octopus taco was so unique.
For breakfast, Bread Alone has an amazing pastry selection, while The Mud Club has very cool outdoor vibes and good (but small) wood-fired bagels.
Just outside of Woodstock, Phoenicia Diner has impeccable mountain views to go with your fries. Their outdoor area is very cute and a great socially-distanced option.
Don’t forget to get your chocolate fix at Fruition. The small-batch chocolate bars are worth the stop but don’t forget about the cookies. Next time remind me to get more than one…
We didn’t get to try Oriole 9, Dixon Road Side, or Cherries Deli but those are also good options depending on how long your stay is.
Not having many other travel options this year was a blessing in disguise because I’m so glad we got to take this little trip! If you or have been comment below anywhere else I should check out if I make it back up there.
On the Way There/Home
There are a ton of great spots to hit if you’re heading up to the Catskills from New York City so definitely take advantage of the drive!
On the west side of the Hudson, you can hike Bear Mountain, stroll Storm King Art Center or check out the grounds at West Point, which are supposed to be beautiful.
On the east side, stop for lunch in a small town like Beacon or Cold Spring. We had a great lunch with pie for dessert at Hudson Hil’s in Cold Spring and had fun browsing the game selection at The Gift Hut on the main street. There was also a very cute local bookstore along with some other shops.
Leave a Reply